Lipids of cultured hepatoma cells: V. Distribution of isomeric monoene fatty acids in individual lipid classes

Monoenoic acid fractions were isolated from phosphatidylcholines, phosphatidylethanolamines, triglycerides, and cholesterol esters derived from minimal deviation hepatoma 7288C cells cultured on 11 media containing varying levels of serums and lipids. Hexadecenoate (16∶1), octadecenoate (18∶1), and eicosenoate (20∶1) fractions were subjected to ozonolysis and the isomeric composition of the monoene fractions determined quantitatively by gas liquid chromatography. The 16∶1 fractions consisted of palmitoleic acid, the Δ9 isomer (85–90%), and the Δ11 isomer (10–15%) in most of the cases; growth media and lipid class origin had little effect upon composition. The predominate acids of the 20∶1 fraction were the Δ13 and Δ11 isomers. Generally, the Δ13 isomer was present in the highest concentration, and this isomer was higher in phosphatidylcholines than the other classes. Vaccenic acid represented 33–66% of the 18∶1 fraction, and the balance was oleic acid. Oleic acid concentrations decreased, and vaccenic acid levels increased as the growth medium serum and lipid levels decreased. Lipid classes did not exhibit any distinct preference for either isomer. These data represent the first quantitative isomeric analysis of monoenoic acids derived from individual lipid classes and are the first to show the occurrence of high levels of vaccenic acid in neoplastic cells. This study suggests that the elevated levels of oleic acid, one of the most frequently observed changes in tumor lipids, may, in fact, represent elevated levels of vaccenic acid.